Water → HCID 54416206, compound

HRID 2399568Notes

Reaction equation

HRID 2399568 reaction equation
[CH3:1][O:2][C@H:3]1[C:8]([CH3:10])([CH3:9])[CH2:7][CH2:6][C@@H:5]([C:11]([CH3:13])=[CH2:12])[C@@H:4]1[C:14](OC)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH3:1][O:2][C@H:3]1[C:8]([CH3:10])([CH3:9])[CH2:7][CH2:6][C@@H:5]([C:11]([CH3:13])=[CH2:12])[C@@H:4]1[CH2:14][OH:15]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57263638HCID 57263638, compound

Product 1

HCID 54416206HCID 54416206, compoundYield 86,157.703%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl (1S,2R,6R)-2-methoxy-3,3-dimethyl-6-(1-methylvinyl)cylcohexane-1-carboxylate (1.03 g) in dry diethyl ether (10 ml) at 0° C., lithium aluminum hydride (92 mg) was added in small portions. The mixture was stirred for 1 hr at room temperature. After the mixture was cooled to 0° C., the mixture was treated by successive dropwise addition of 92 ml of water, 92 ml of 15% sodium hydroxide solution and 276 ml of water. The resulting granular white precipitate was filtered, and the filtrate was concentrated to give (1R,2R,6R)-[2-methoxy-3,3-dimethyl-6-(1-methylvinyl)cyclohexyl]methanol (784 g, 91% yield).

Workup

  1. temperatureAfter the mixture was cooled to 0° C.
  2. filtrationThe resulting granular white precipitate was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ec498bb8ea3740f7a0e0a5af5bbb5314
Source dataset
uspto-grants-1995_09
Patent number
US05449785

Reaction notes

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